(4aS,8R,8aR,9aS)-8,9a-dihydroxy-3,8a-dimethyl-5-methylidene-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one

Details

• Internal ID: 2ff29c7e-89ec-4b38-aa4a-f6baa40f2f37
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (4aS,8R,8aR,9aS)-8,9a-dihydroxy-3,8a-dimethyl-5-methylidene-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1=C2CC3C(=C)CCC(C3(CC2(OC1=O)O)C)O
• SMILES (Isomeric): CC1=C2C[C@H]3C(=C)CC[C@H]([C@@]3(C[C@@]2(OC1=O)O)C)O
• InChI: InChI=1S/C15H20O4/c1-8-4-5-12(16)14(3)7-15(18)11(6-10(8)14)9(2)13(17)19-15/h10,12,16,18H,1,4-7H2,2-3H3/t10-,12+,14+,15-/m0/s1
• InChI Key: WSGUEAHXLYQKIH-BTQDYEIMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.68
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9922	99.22%
Caco-2	+	0.6830	68.30%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7291	72.91%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.9015	90.15%
OATP1B3 inhibitior	+	0.8850	88.50%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5670	56.70%
BSEP inhibitior	-	0.7491	74.91%
P-glycoprotein inhibitior	-	0.9326	93.26%
P-glycoprotein substrate	-	0.8453	84.53%
CYP3A4 substrate	+	0.6462	64.62%
CYP2C9 substrate	-	0.7943	79.43%
CYP2D6 substrate	-	0.8686	86.86%
CYP3A4 inhibition	-	0.5785	57.85%
CYP2C9 inhibition	-	0.9102	91.02%
CYP2C19 inhibition	-	0.8956	89.56%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.6427	64.27%
CYP2C8 inhibition	-	0.8280	82.80%
CYP inhibitory promiscuity	-	0.9161	91.61%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4673	46.73%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.8752	87.52%
Skin irritation	+	0.6359	63.59%
Skin corrosion	-	0.9012	90.12%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6422	64.22%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.6783	67.83%
skin sensitisation	-	0.7869	78.69%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.5842	58.42%
Acute Oral Toxicity (c)	I	0.4493	44.93%
Estrogen receptor binding	-	0.5325	53.25%
Androgen receptor binding	+	0.6500	65.00%
Thyroid receptor binding	+	0.6667	66.67%
Glucocorticoid receptor binding	+	0.6893	68.93%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6211	62.11%
Honey bee toxicity	-	0.8761	87.61%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9957	99.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.89%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.83%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.29%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.68%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.85%	89.00%
CHEMBL1871	P10275	Androgen Receptor	86.89%	96.43%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.78%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.41%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.44%	97.09%
CHEMBL1902	P62942	FK506-binding protein 1A	82.05%	97.05%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.94%	97.25%

Plants that contains it

• Licaria triandra
• Smyrnium olusatrum

Cross-Links

• PubChem: 12009778
• LOTUS: LTS0258734
• wikiData: Q105311848